N-dodecyl-2,2,2-trifluoroacetamide | 1959-54-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-dodecyl-2,2,2-trifluoroacetamide
• 英文别名: N-Dodecyltrifluoracetamid
• CAS: 1959-54-2
• 化学式: C₁₄H₂₆F₃NO
• 分子量: 281.362
• InChiKey: GDHYSHGLRHWHDX-UHFFFAOYSA-N

物化性质

• 沸点：
  328.3±42.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-dodecyl-2,2,2-trifluoroacetamide 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2,2,2-trifluoroethyl)dodecylamine
  参考文献：
  名称：

  Lysosomotropic agents. 1. Synthesis and cytotoxic action of lysosomotropic detergents

  摘要：

  Amines whose pK values lie between about 5 and 9 are lysosomotropic because lysosomes are acidic intracellular compartments. If such amines bear long hydrophobic chains, they become detergents upon protonation inside the lysosomes, rupturing the lysosomal membrane and killing the cell. Six types of lysosomotropic amines have been prepared that all behave in the expected manner. They are cytotoxic to all lysosome-bearing cells but not red blood cells, which lack lysosomes. Their mode of action, the effect of alkyl chain length on activity, and the fact that their cytotoxic action appears only above a threshhold intracellular concentration support the belief that they behave as lysosomotropic detergents. Among the potential applications is cancer chemotherapy.

  DOI：

  10.1021/jm00195a026
• 作为产物：
  描述：

  十二烷基伯胺 、 三氟乙酸乙酯 在 lanthanum(lll) triflate 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 以83%的产率得到N-dodecyl-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Efficient DBU accelerated synthesis of ¹⁸F-labelled trifluoroacetamides

  摘要：

  溴二氟乙酰胺的亲核性¹⁸F-氟化反应在DBU存在下进行。提出了DBU作为有机中介的机理。

  DOI：

  10.1039/c6cc08535k

文献信息

• Carbon–Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)–CF₃ Bond Cleavage
  作者：Longzhi Zhu、Liyuan Le、Mingpan Yan、Chak-Tong Au、Renhua Qiu、Nobuaki Kambe

  DOI：10.1021/acs.joc.9b00583

  日期：2019.5.3

  The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF3 group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily available trifluoroacetyl amides can be conveniently obtained and used as new versatile precursors for isocyanates

  描述了三氟乙酰酰胺与格氏试剂的反应，以用各种烷基或芳基取代CF 3基团。各种芳基，喹啉-8-基和（杂）烷基官能团以及F，Cl和Br原子均具有良好的耐受性。这些水分稳定且易于获得的三氟乙酰基酰胺可以方便地获得，并用作异氰酸酯的新型通用前体。对照实验表明，反应是通过异氰酸酯中间体和/或醇盐/酰胺双阴离子中间体进行的。
• Lysosometropic detergent therapeutic agents
  申请人：Merck & Co., Inc.

  公开号：US04719312A1

  公开（公告）日：1988-01-12

  The present invention is concerned with the preparation of lysosomotropic detergent agents and pharmaceutical composition useful in the treatment of cancer. These compounds are amine derivatives having a pK of 3.5 of the general structure ##STR1## in which R.sub.1 is C.sub.8-30 alkyl, C.sub.8-30 -alkenyl, substituted C.sub.4-30 alkyl or substituted C.sub.4-30 -alkenyl; R.sub.2 is hydrogen or C.sub.1-4 alkyl and Y is an electron withdrawing group, to control the pK, selected from trifluoroethyl, and difluoroethyl.

  本发明涉及制备溶酶体靶向性清洁剂剂和用于癌症治疗的药物组合物。这些化合物是具有pK值为3.5的胺衍生物，其一般结构为##STR1##其中R.sub.1为C.sub.8-30烷基，C.sub.8-30烯基，取代的C.sub.4-30烷基或取代的C.sub.4-30烯基；R.sub.2为氢或C.sub.1-4烷基，Y为电子吸引基，以控制pK值，所选自三氟乙基和二氟乙基。
• Lysosomotropic fluorinated amine therapeutic agents and compositions containing them
  申请人：Merck & Co., Inc.

  公开号：EP0009944A2

  公开（公告）日：1980-04-16

  Compositions useful in the control of fertility, the inhibition of malignant cell growth, and the control of other diseases which accumulate macrophages at the disease site, comprising a pharmaceutical carrier and lysosomotropic substance comprising a weakly basic amine of pK 4.5 to 9 containing at least one hydrophobic substituent or a peptide conjugate hydrolyzable by lysosomal enzymes to a biologically active substance. Certain of the amines, viz. those of formula : in which R is an alkyl substituent of from 8-30 carbon atoms, R is hydrogen or alkyl, and R2 is fluoroloweralkyl of 2-3 carbons, are novel and constitute another embodiment of the present invention. The compositions of the present invention are used to inhibit or alter the function of lysosome-bearing cells.

  可用于控制生育、抑制恶性细胞生长和控制在疾病部位聚集巨噬细胞的其他疾病的组合物，包括药物载体和溶酶体促进物质，溶酶体促进物质包括pK 4.5至9的弱碱性胺，其中含有至少一个疏水取代基，或可被溶酶体酶水解为生物活性物质的肽轭合物。 某些胺，即式中：R为8-30个碳原子的烷基取代基，R为氢或烷基，R2为2-3个碳原子的氟代烷基的胺，是新颖的，构成本发明的另一个实施方案。 本发明的组合物用于抑制或改变含溶酶体细胞的功能。
• US4719312A
  申请人：——

  公开号：US4719312A

  公开（公告）日：1988-01-12
• Efficient DBU accelerated synthesis of ¹⁸F-labelled trifluoroacetamides
  作者：Antonio Bermejo Gómez、Miguel A. Cortés González、Marvin Lübcke、Magnus J. Johansson、Christer Halldin、Kálmán J. Szabó、Magnus Schou

  DOI：10.1039/c6cc08535k

  日期：——

  Nucleophilic ¹⁸F-fluorination of bromodifluoroacetamides was performed in the presence of DBU. A mechanism where DBU acts as organomediator is proposed.

  溴二氟乙酰胺的亲核性¹⁸F-氟化反应在DBU存在下进行。提出了DBU作为有机中介的机理。